Who had the most saddest moments in Naruto?

[Raijingan]

I pick out Lee.

Yes Lee. His flashback during the gaara scene + sadness and sorrow was heartbreaking and heartwarming at the same time

 

[LOCKKO REE]

obito was about to kiss rin's pic but kakashi confronted... what a sad moment XD

 

[Dr Ramen]

Asuma, Jiraiya and Itachi